Holiday rentals in Cutler Bay

Boutique Style House Hot-Tub Mini-Golf BBQ & Games

Come enjoy this beautiful vacation townhouse with 3 bedrooms, 2.5 bathrooms in Homestead - Miami with a large parking driveway. This is a tropical paradise close to everything needed to live the good life! Great location close to Miami Zoo, Homestead Speedway, and US1 to the Florida Keys The property sleeps up to 8 guests and is ideal for a group of friends or family looking to experience all the sunshine and fun that South Florida has to offer. Property is located in 137 Avenue and 260th Lane

King Bed Home by the Bay FAST WI-FI & Coffee

Whether you are visiting the Florida Keys, the beaches of Miami, or looking for a comfortable staycation, discover what South Florida has to offer while feeling at home. You'll be located near Southland Mall, The Falls Shopping Center, Black Point Marina, Miami Metro Zoo, Deering Estates, the Dennis C. Moss Arts Center and more! ❧ 48 minutes from the Florida Keys. ❧ 37 minutes from Miami Beach. ❧ 33 minutes from the Everglades. Message us about long stay, military, & first responder discounts.

Beautiful Family Villa. Large Outdoor Space & BBQ

Spacious 4BR, 2BA home in Cutler Bay with 5 comfy beds, full kitchen, washer & dryer, and a massive backyard! Enjoy the oversized outdoor space — perfect for playing sports, barbecues, or relaxing under the sun. Located in a peaceful area near shops, parks, and Black Point Marina. Ideal for families and groups seeking comfort, privacy, and a true South Florida experience. The home offers free parking, fast Wi-Fi, smart TVs, and plenty of room to unwind and make lasting memories together.

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

🏡 Spacious Home with Heated Pool, BBQ & Game Room 🎉 Enjoy this perfect getaway for families and groups! 🛏 4 bedrooms: King, 2 Queen, and a bunk bed (Full + 2 Twin). 🚿 2.5 bathrooms. 🎱 Game room with pool table. 📺 TVs in all rooms, living room & patio. 👶 Crib & high chair available. 🍽 Fully equipped kitchen. 🏊‍♂️ Private heated pool 🔥. 🍖 BBQ & 🌿 2 hammocks in the patio. 🏠 Spacious, cozy, and perfect for relaxation. Book now for an unforgettable stay! ✨

Lake Of Dreams Miami House - The Perfect Place

Immerse yourself and your family in the ideal mix of rustic charm and contemporary comfort in our unique farmhouse-style retreat, located in Miami. The expansive yard, featuring comfortable lounge chairs, is perfect for relaxing and basking in the sun by the inviting pool Our stunning private lagoon offer a serene escape from the everyday hustle. The crystal-clear waters and cascading waterfalls create a peaceful ambiance, perfect for relaxation.

Waterfront Miami Villa | Pool, Kayaks, Mini Golf

Escape to this stunning waterfront villa, perfect for families and groups up to 11. Set along a peaceful canal, this private retreat blends relaxation and adventure with direct water access and resort-style amenities. Resort-Style Highlights: • Heated private pool • Complimentary kayaks & life jackets • Mini golf & outdoor lounging • Smart TVs, fast WiFi, and modern interiors Minutes from Black Point Marina, Miami, and the Florida Keys.

4BR Home with Pool, Playground & Boat/RV Parking

Beautiful Cutler Bay pool home with large backyard, boat/rv parking, and playground. Whether you're planning a getaway to the Florida Keys, soaking up the sun on the beaches of Miami, or just looking for a cozy staycation, this home is your perfect launchpad for everything South Florida has to offer. • The Florida Keys – 48 minutes • Miami Beach – 37 minutes • Everglades National Park – 33 minutes

Perfect 3 bedroom Home for Miami Getaway

Relax in this cozy, fully equipped home featuring a spacious living area, modern kitchen, and comfortable bedrooms ideal for families or small groups. Perfectly located just steps from Old Cutler Road, surrounded by unique dining, shopping, and top attractions like Southland Mall, The Falls, Black Point Marina, Deering Estates, Everglades National Park, and Miami Beach.

Chicness-Oasis FIFA World Cup 2026 • Near Stadium

Welcome to your dream escape! A boho chic retreat blending laid-back luxury with natural charm. This haven features an open-plan living area, sunlit pool deck with plush daybeds, and a lush backyard with a whimsical tree swing. Thoughtfully designed for relaxation and style—perfect for families, couples, or creatives seeking a soulful getaway.

Paradise Home/Ideal Families /Grill / Bar

1- 3 Bedrooms (Sleeps 8 People) (1 King Bed, 1 Bunk Bed, 1 Twin Bed) 2- 25 Min to Key Largo 3- 25 Min to Miami Beach 4- 10 Min to Miami Metro Zoo 5- Homestead Speed Way 6- Private Parking 2 Cars 7- Fast Wifi 8- Laundry In Unit 9- Barbecue and Bar 10- Outdoor Dinning Area 11- Fully Equipped Kitchen 12- Ideal for Families

Royal Palm Gateway - Modern 4BR Homestead Retreat

Welcome to Royal Palm Gateway, a 4-bedroom, 2.5-bath family retreat in Homestead, Florida! Enjoy modern design, spacious two-story living, natural light, and relaxing outdoor areas. Ideal for multi-generation trips, families, and boaters, this elegant retreat offers comfort, convenience, and a memorable Florida escape.